반응 #1244258

반응 방정식

NaOH

H-Glu-Glu Adamantane

β-cyclodextrin DTBP

Z-Glu(Bn)-OSu

H-Glu(Bn)-OH

sodium bicarbonate

→

solid 6

β-cyclodextrin

용매

THF

THF

CH3CN

water

반응 조건

후처리

1. 1
   기타THF and CH3CN was evaporated under high vacuum
2. 2
   workup.ADDITIONTo the aqueous mixture was added 1 N HCl
3. 3
   기타Precipitation
4. 4
   추출The mixture was extracted with chloroform
5. 5
   건조The organic phase was dried with MgSO4
6. 6
   기타MgSO4 was removed by filtration
7. 7
   기타Organic solvent was evaporated

실험 절차

Compound numbers below refer to the above scheme. I. Synthesis of H-Glu-Glu-Adamantane 7. H-Glu(Bn)-OH (3.55 g, 15 mmol) was dissolved in water (16 mL) containing sodium bicarbonate (1.26 g, 15 mmol). To the mixture was added Z-Glu(Bn)-OSu (4.68 g, 10 mmol) in THF (30 mL). To the mixture was added another 30 mL THF, 20 mL CH3CN and then 2N NaOH 10 mL. The solution was stirred for 16 hours at room temperature. THF and CH3CN was evaporated under high vacuum. To the aqueous mixture was added 1 N HCl to adjust the pH to 3. Precipitation was observed. The mixture was extracted with chloroform. (3×30 mL). The organic phase was dried with MgSO4. MgSO4 was removed by filtration. Organic solvent was evaporated to give white sticky solid 6. 6 was used for next step reaction without further purification.

출처